Water → HCID 86692596, compound

HRID 1748655Notes

Reaction equation

HRID 1748655 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][N:15]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4].[CH2:22](I)[CH3:23].O>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][O:21][CH2:22][CH3:23])=[CH:16][N:15]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 86692597HCID 86692597, compound

Product 1

HCID 86692596HCID 86692596, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (175 mg) was added at room temperature to a solution of 1-[5-(hydroxymethyl)pyridin-2-yl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (935 mg) described in Reference Example 41(3) in N,N-dimethylformamide (18 ml), and stirred at the same temperature for 30 minutes. Ethyl iodide (0.6 ml) was added and the mixture was stirred at 80° C. for two hours. Then, Sodium hydride (175 mg) and ethyl iodide (0.6 ml) were added and stirred at 80° C. for two hours. After the reaction, the reaction solution was cooled to room temperature, water was added and extracted with ethyl acetate four times. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, and the residue was purified with a silica gel column chromatography (n-hexane/ethyl acetate) to give 1-[5-(ethoxymethyl)pyridin-2-yl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (223 mg) as a white solid.

Workup

  1. stirringthe mixture was stirred at 80° C. for two hours
  2. stirringstirred at 80° C. for two hours
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate four times
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customthe residue was purified with a silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9714e0b4401548bdad825fa129f5c739
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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